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<h1><a href="https://archiveofourown.org/works/27306583">A Sunset, A Secret II</a> by <a class='authorlink' href='https://archiveofourown.org/users/Hardwontoegold55/pseuds/Hardwontoegold55'>Hardwontoegold55</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>CollegeHumor, Drawfee RPF, Drawga, Headgum - Fandom, Headgum Podcasts - Fandom, NADDPOD - Fandom</td></tr>

<tr><td><b>Genre:</b></td><td>Caldwell Tanner - Freeform, Comments welcome :-), Headgum, Headgum Podcasts, Jake and Caldwell at it again, M/M, One Shot, Sex, Short One Shot, Smut, college humor - Freeform, collegehumor - Freeform, jake hurwitz - Freeform, naddpod, not another dnd podcast - Freeform</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-10-31</td></tr>

<tr><td><b>Updated:</b></td><td>2020-10-31</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-06 19:55:58</td></tr>

<tr><td><b>Rating:</b></td><td>Mature</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>1,659</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/27306583</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/Hardwontoegold55/pseuds/Hardwontoegold55</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Caldwell comes across the country to finish a business deal with Jake, and the celebration quickly becomes physical...</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>jake hurwitz/caldwell tanner</td></tr>

<tr><td><b>Kudos:</b></td><td>4</td></tr>

</table>

<a name="section0001"><h2>A Sunset, A Secret II</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>Back with more smut... idk about y’all there ain’t much else to do now a days XD</p>
    </blockquote></div><div class="userstuff module">
    
    <p>“Cheers, dude!” Jake said as he raised the bottle of craft beer he had just popped the cap off.  “Uh that’s a big 10-4 buddy!”  Caldwell said as he finished the salute by clicking his bottle against Jake’s proffered one.  </p><p>The chime of glass was a beautiful noise to the two men, who stood over an open laptop in Jake’s home office as the Friday sunset over New York City behind them.  “It took all goddamn week to sort it, but we did it. What a feeling.”  Jake tossed his mane of sandy blonde hair back as he dragged a weary but triumphant hand down his lightly bearded cheek.  </p><p>Caldwell took a seat back in front of the laptop, trying to make himself not watch Jake so closely by taking a swig of his own and reviewing their work.  A huge new merch order for their DND podcast had just been finalized.  It was their most ambitious one yet, and Caldwell had been the lead designer on every single item, from dice sleeves to sketchbooks.  He had flown out to New York for a week and a half to work as closely with Jake, the brains behind the business, as closely as possible to ensure everything went smoothly.  They had been poring over design concepts and samples, writing back notes and having conference calls.  But now the confirmation notice in Jake’s email meant they had succeeded.  With time to spare no less!  Just the two of them, shoulder to shoulder.  It felt like old times. Very old times.</p><p>“So how do we celebrate, I’m so exhausted but so amped!!”  Caldwell could feel his head buzzing, but his limbs were heavy.  A night on the town could wait, perhaps. </p><p>“I’ve already got the ‘za order in, my man.  We’re taking it easy tonight.  Now come on, help me get this champagne open, i’m a klutz.”</p><p>“Hah, yea, it's like you have crab claws or something.”</p><p>“Don’t joke about that.”</p><p>--</p><p>Sometime later, over a half empty pizza box, a drained bottle of champagne, and several more beer bottles, Jake and Caldwell found themselves lazily sprawled on Jake’s couch, idly watching the credits roll over “Dungeons &amp; Dragons: Wrath of the Dragon God.”  Both of them were amazingly content, feeling warm and accomplished and happy to share the victory.  Jake looked over and saw a smile that bordered on Smug on Caldwell’s face.  One of his arms was thrown back over his head, revealing just a sliver of skin on his tummy where his shirt followed up.  He felt a pulse in his loins and shifted.  “Hey…” Jake whispered slowly.  The last rays of the sun had just been occluded by the buildings around them, so as Caldwell turned, he saw Jake’s face illuminated in the cold glow of the TV, which revealed everything with a deft flatness.  The brunettes’ eyes widened.  “Hey yourself.”</p><p>--</p><p>They had moved toward each other at the same time, and briefly crashed into a hungry kiss on the couch, but the momentum of their passion brought both men up, still locked at the lips, Caldwell’s hands finding Jake’s silky hair and the curve of his hip against his athleisure shorts.</p><p>Breaking silently, they moved to the guest bedroom Caldwell had been staying in. Caldwell takes Jake by the hand and leads him.  Playfully, Jake tackles Caldwell to the mattress and grbas him in a headlock.  The heat of Jake’s body, his laughter ringing through his chest and into Caldwell’s ears, and the clean manly smell of his armpits was driving Caldwell wild.  His 4” cock was tight against his boxer briefs as he broke out of the head lock and clambered on top of Jake, pinning him in a kiss and feeling hands wander over his back and ass.  </p><p>In almost a blur they were both naked, whirling limbs shedding clothes as fast as possible.</p><p>Caldwell began positioning himself under Jake, moving his legs to entangle his lover and pull him closer. Jake broke their kiss and whispered huskily into Caldwell’s neck; his golden eyes glinted as he spoke which sent goosebumps all along Caldwell’s arms and back.<br/>
“Something else tonight… roll over…” Jake said in a low breathy voice as he ran his hands up and down Caldwell’s sides in an intimate gesture. </p><p>With our even a nod Caldwell complied, deep in passion and wanting Jake any way Jake wanted him. They move at the same time: Jake rising back up on his knees on the bed, shrugging off Caldwell’s legs and absentmindedly stroking himself. Caldwell gracefully rolling over and repositioning himself in front of the sand haired brunette, on all fours with his back slightly arched, narrow hips swaying slightly as his smaller cock leaked passion onto the sheets. </p><p>The ambient light of night time NYC cast irregular, upward shadows in a carousel of hues into the room. But Jake could see all of Caldwell, how he presented himself with the upturn of his back and how his lithe  shoulders were rising and lowering with simmering arousal.  Most of all, Jake could see Caldwell’s rosy pink hole, a narrow slit ringed by gently wrinkling skin. It had been cleaned and groomed, which made Jake smirk. The darker haired man had been ready for him. Jake placed the hand he had been stroking himself on Caldwell’s hip, and brought himself close enough to feel the heat off Caldwell’s body. Caldwell moaned and brought himself backwards automatically, they were now gently grinding with Jake’s girthy 7.5” nestled between his skinny cheeks. </p><p>Jake brought his other hand around, and placed two fingers below Caldwell’s lower lip, gently stroking his handsome chin in silent instruction. Caldwell obliged, bringing his lover’s fingers into his mouth and costing them with his own spit. He could hear and feel the low growl of appreciation from Jake, still steadily Rocking his cock against Caldwell’s ass. Jake pulled the fingers back, and pulling himself back from Caldwell set to work with his newly Slicked fingers.  Caldwell hitched at this direct touch, feeling Jake’s fingers probe him slowly. He raised his head and made short gasps slog arousal as Jake sank his first knuckles in.<br/>
“Just relax, babe, you’re doing so good… you always do…” Jake cooed, watching his fingers slowly disappear into Caldwell. His cock was harder than steel, and the dark red tip looked eager to follow his finger’s lead. Jake spat a blob of his own spit onto the point he and Caldwell joined, finishing sinking both fingers all the way in. Caldwell mined loudly as Jake’s fingers began to move and twist, loosening him up and finding tender bundles of nerve.</p><p>A few minutes of this, and then Jake softly said “Ready?”  “Ready” Caldwell said quickly, his brow furrowed and sweat dripping from his face as he felt Jake slowly prepare him.  Every time Jake brushed his prostate, he could feel a fire in his stomach that he knew he needed stoked.</p><p>Jake drew his fingers out, causing Caldwell to gasp, and moved in closer, lining his own drooling cokhead up with Caldwell’s slightly winking hole.  Caldwell cast a look back over his shoulder, and in that moment Jake looked forward to watch his lover.  Their eyes locked as Jake pushed through the sensitive ring of muscle, and Caldwell saw stars for a brief moment.  </p><p>Slowly Jake worked the full length of his cock in Caldwell, who was moaning wiggling with pleasure. “Deeper, go on, go on, please!” Caldwel pleaded in lusty gasps. Finally, Jake bottomed out and Caldwell could feel the soft brush of his neatly maintained pubes against his bare cheeks.  For a minute they stayed there, both of them getting their breathing, their elevated pulses sending reverberating waves of pleasure as they tightened and expanded against each other.  </p><p>“I’m gonna start.” Jake said in a gruff voice, deep with lust.  Caldwell felt two hands grip his hips firmly.  His cock twitched and he assented with a moan. Jake withdrew half way at first, slowly gliding in and out, watching Caldwell’s hole react to his member.  He lobbed another globe of spit onto himself, aiding the process as he drove back in.  Soon, he was pulling almost all the way out on each stroke, and he could feel Caldwell going cravy below him.  Jake had maneuvered an old pillow below his bottoms’ hips for support, and now Caldwell was grinding into iron each thrust.  He must be going crazy, Jake thought to himself, which caused his cock to harden even more and his pace to increase.  </p><p>Caldwell knew he didn’t have much more time left in him.  “Jake… Please… I need it…” he said, his face half turned and pressing into the sheets.  He bucked his hips back up on each thrust now, in emphasis.</p><p>He was rewarded when wordlessly, Jake moved his hand from Caldwell’s hip, sliding it up and under him to grab his hopelessly slick and hard dick.  Jake felt how much he had leaked while being fucked, and felt a haze of lust settle over him.  A few quick, expert strokes by Jake and Caldwell felt the fire in his stomach rise uncontrollably.  “OH MY GOD, OH MY GOD, JAKE YES OH MY GOD!” Caldwell exclaimed as he unloaded 10 huge shots of cum all over Jake’s hand, the pillow and the sheets.  Those spurts were met by equally powerful spasms in Caldwell’s whole body, which clamped down on Jake’s rock hard dick like a vice.  Jake felt himself push over the edge as his Lover’s body milked the cum out of him.  He collapsed against Cadlwell’s sweaty back, his own chest and forehead sweat mingling as he gently bit his lover's neck and ruffled his hair.  They were both sweaty, exhausted, and covered in cum; laying in an intimate afterglow of pure bliss.<br/>
Later, as they washed each other playfully in the shower, Jake said “Is there any pizza left?” and they both laughed.</p>
  </div><div class="fff_chapter_notes fff_foot_notes"><b>Author's Note:</b><blockquote class="userstuff"><p>Hello! If you read the story, please consider leaving me a comment! Criticism, repudiation, and praise are all welcome.</p></blockquote></div></div>
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